When Friends Win and Lose at Investing: Why Do I Feel This Way?

A while back I started a group chat with a few friends and mutual acquaintances focused entirely on investing. The idea was simple: create a space where we could share insights, discuss market moves, ask questions, and hopefully grow together financially. I didn’t expect the experience to become so personal — or so revealing.

What started as a fun initiative quickly became a mirror, showing me things I didn’t expect to see in myself. Not about investment strategies, but about emotions. About how I feel when others in the group make or lose money. And, more honestly, how I feel about my own choices when compared to theirs.

The Strange Satisfaction of Watching Others Lose

I’ll start with something uncomfortable: I find a strange sense of satisfaction when someone in the group talks about an investment that didn’t go as planned.

One member shared that they had either owned Apple or Microsoft a few years ago — two of the most iconic, steady-growing tech giants — but they sold before the bull run that multiplied those stocks five times over. I remember listening on the conversation and feeling a weird mix of empathy and… relief?

Part of me genuinely felt bad. They missed out on a massive gain. That sucks, and I knew they were kicking themselves over it. But another part of me felt validated. I still own Apple and Microsoft. I chose not to sell. And in that moment, their “mistake” reinforced my decision as the “right” one.

And I had to ask myself: Why do I feel good when someone else gets it wrong?

Is this what investing does to us — turns everything into a scoreboard?

When Friends Win, Why Do I Feel Like I’m Losing?

It’s not just when people lose that I feel something. It’s also when they win.

Take another example: A friend bought more Nvidia stock before it doubled in 2025. I was happy for them. Really, I was. But I also felt this twinge of regret, maybe even envy. Why didn’t I buy more? Why didn’t I see it coming? Why do I feel like I missed out — even though I made money elsewhere?

I know it’s irrational. There will always be another winning stock, another trade I didn’t make, another opportunity someone else capitalized on. But emotionally, it’s hard not to measure my performance against those around me — especially when those people are right there in a group chat, sharing their moves in real-time.

It makes me ask: Why can’t I just be happy for people without turning it into a reflection on myself?

The Investment Mirror: What It Really Reflects

I think investing is uniquely tied to identity. We don’t just choose stocks — we make judgments. We weigh risks. We time entries and exits. And when we’re right, it feels like a reward for our intelligence, patience, and foresight.

But when we’re wrong — or when someone else is more right than we were — it cuts a little deeper than a simple financial miss. It can feel like a reflection of our judgment. Like we’ve fallen behind in a race we didn’t even realize we were running.

When you invest with friends, the comparison becomes more personal. You know these people. You share your wins and losses. Their success isn’t just an anonymous headline on CNBC — it’s in your face, on your screen, in your chat. And that proximity makes their decisions feel more relevant to your own.

You start comparing — and comparing leads to questioning.

Did I sell too early?
Did I buy the wrong stock?
Should I have known better?

Investing Isn’t a Competition… But It Feels Like One

In theory, investing isn’t supposed to be a competition. Everyone has their own goals, timelines, and risk tolerances. One person might be investing for early retirement, another for generational wealth, and another just trying not to lose money.

But the moment we start tracking our returns against someone else’s, it feels like a leaderboard. And suddenly, their win feels like your loss. Their mistake feels like your validation.

I’ve realized that I often use others’ failures as confirmation that I made the right call. And when others succeed, I sometimes take it as evidence that I messed up — even if I didn’t.

This isn’t just about stocks. It’s about ego.

It’s about the need to be right. To be the one who saw the trend before it was obvious. To be the smart investor.

And maybe, deep down, it’s about fear — fear that we aren’t as good at this as we think. That our wins were luck. That next time, we might be the one telling the group, “Yeah… I sold too early.”

The Truth: We Can’t Own Everything

Here’s a reality that’s easy to forget in the middle of comparison: you can’t own every winning stock.

Nobody does.

Even the greatest investors of all time — Buffett, Lynch, Druckenmiller — missed out on huge gains. They made bad calls. They sold early. They passed on life-changing opportunities. And yet, they still did exceptionally well. Because investing isn’t about being right all the time. It’s about being consistent. Disciplined. Strategic.

You have to pick and choose. That’s the nature of the game.

So if a friend crushed it with Nvidia and I didn’t — it doesn’t mean I failed. Maybe I was focused on another sector. Maybe I was overexposed to tech already. Maybe I made the decision that was right for me based on the data I had.

That doesn’t mean I should feel bad about it.

It just means that was their move, and I made mine.

Rewiring the Emotional Response

I think part of growing as an investor — and as a person — is rewiring how we respond emotionally to others’ wins and losses.

Here’s what I’ve been working on:

1. Detach ego from outcomes.
Just because someone made a different move doesn’t make them smarter or dumber. It just makes them different. Everyone’s playing a slightly different game.

2. Celebrate others without comparing.
When someone wins big, let that be a data point, not a judgment. Be happy for them. Learn from it. But don’t let it overshadow your own path.

3. Learn from others’ mistakes with empathy.
When someone makes a bad call, don’t secretly rejoice. Use it as a learning opportunity. Reflect on what led to that decision — and how you might avoid it yourself. But don’t root for it. That’s not the energy you want to carry.

4. Zoom out.
Your portfolio is a long-term story, not a highlight reel of daily wins and losses. If you’re up over 10 or 20 years, who cares if someone doubled their money on a hot stock last quarter?

5. Remember your ‘why’.
You invest for your reasons. Maybe it’s early retirement. Maybe it’s freedom. Maybe it’s generational wealth. Stay focused on that — not someone else’s scoreboard.

The Point of the Group Chat

When I started the investment group chat, I hoped it would help us all get smarter. Share ideas. Catch each other’s blind spots. Be better together.

But it’s also been a crash course in emotional management.

Because investing isn’t just about analysis — it’s about psychology. And in a group of people you respect, admire, and sometimes secretly compete with, that psychology gets complicated fast.

The real challenge isn’t just picking the right stocks — it’s being the kind of person who can celebrate others’ wins, empathize with their losses, and stay grounded in their own journey.

Final Thoughts

I’ll admit it: I’m still working on this. I still feel a bit better when someone else messes up — and a bit worse when someone else makes a big win I missed.

But I’m learning.

Because if the ultimate goal of investing is financial freedom, then emotional freedom needs to be part of the package. I don’t want to be someone whose self-worth rises and falls with the tickers in my group chat. I want to build wealth and peace of mind.

So here’s to letting go of the need to always be right.
Here’s to learning from each other without judgment.
Here’s to investing not just in stocks, but in mindset.

And if I miss a 10x stock along the way… that’s okay.

I probably caught another one someone else didn’t.

And that’s the game.